#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:30:50 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179249 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/69/4316912.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4316912
loop_
_publ_author_name
'Cheng-Han Yang'
'Juan Beltran'
'Vincent Lemaur'
'Jérôme Cornil'
'David Hartmann'
'Wiebke Sarfert'
'Roland Fröhlich'
'Claudia Bizzarri'
'Luisa De Cola'
_publ_section_title
;
 Iridium Metal Complexes Containing N-Heterocyclic Carbene Ligands for
 Blue-Light-Emitting Electrochemical Cells
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9891
_journal_page_last               9901
_journal_paper_doi               10.1021/ic1009253
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C33 H27 F10 Ir N7 P'
_chemical_formula_weight         934.79
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.963(1)
_cell_angle_beta                 110.194(1)
_cell_angle_gamma                103.789(1)
_cell_formula_units_Z            2
_cell_length_a                   10.2009(2)
_cell_length_b                   13.0257(3)
_cell_length_c                   14.7272(3)
_cell_measurement_reflns_used    5556
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      0.41
_cell_volume                     1738.62(7)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19786
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    3.975
_exptl_absorpt_correction_T_max  0.7683
_exptl_absorpt_correction_T_min  0.3367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.784
_refine_diff_density_min         -1.674
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         8382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0582P)²+3.7990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                7534
_reflns_number_total             8382
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic1009253_si_002.cif
_cod_data_source_block           fro5073
_cod_original_cell_volume        1738.61(6)
_cod_database_code               4316912
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.247166(17) 0.314507(13) 0.184221(11) 0.02777(7) Uani 1 1 d . . .
C1 C 0.1275(5) 0.3854(4) 0.2511(3) 0.0319(9) Uani 1 1 d . . .
N2 N 0.1261(5) 0.4881(3) 0.2770(3) 0.0357(8) Uani 1 1 d . . .
C3 C 0.0224(6) 0.4911(5) 0.3177(4) 0.0447(12) Uani 1 1 d . . .
H3 H 0.0020 0.5534 0.3410 0.054 Uiso 1 1 calc R . .
C4 C -0.0427(6) 0.3895(5) 0.3175(4) 0.0418(11) Uani 1 1 d . . .
H4 H -0.1176 0.3661 0.3404 0.050 Uiso 1 1 calc R . .
N5 N 0.0222(4) 0.3250(3) 0.2765(3) 0.0355(8) Uani 1 1 d . . .
C6 C -0.0281(5) 0.2075(4) 0.2537(4) 0.0397(11) Uani 1 1 d . . .
H6A H -0.0812 0.1803 0.1819 0.048 Uiso 1 1 calc R . .
H6B H -0.0957 0.1829 0.2859 0.048 Uiso 1 1 calc R . .
N7 N 0.0946(4) 0.1643(3) 0.2877(3) 0.0353(8) Uani 1 1 d . . .
C8 C 0.1016(7) 0.0872(5) 0.3445(4) 0.0458(12) Uani 1 1 d . . .
H8 H 0.0331 0.0574 0.3708 0.055 Uiso 1 1 calc R . .
C9 C 0.2258(7) 0.0638(5) 0.3543(4) 0.0490(13) Uani 1 1 d . . .
H9 H 0.2615 0.0138 0.3891 0.059 Uiso 1 1 calc R . .
N10 N 0.2920(5) 0.1267(3) 0.3037(3) 0.0383(9) Uani 1 1 d . . .
C11 C 0.2116(5) 0.1899(4) 0.2605(3) 0.0333(9) Uani 1 1 d . . .
C12 C 0.2170(8) 0.5857(4) 0.2643(5) 0.0516(14) Uani 1 1 d . . .
H12A H 0.3174 0.5838 0.2855 0.077 Uiso 1 1 calc R . .
H12B H 0.2129 0.6491 0.3040 0.077 Uiso 1 1 calc R . .
H12C H 0.1810 0.5891 0.1949 0.077 Uiso 1 1 calc R . .
C13 C 0.4315(7) 0.1212(5) 0.3019(5) 0.0543(15) Uani 1 1 d . . .
H13A H 0.4167 0.0849 0.2360 0.081 Uiso 1 1 calc R . .
H13B H 0.4730 0.0809 0.3497 0.081 Uiso 1 1 calc R . .
H13C H 0.4979 0.1940 0.3186 0.081 Uiso 1 1 calc R . .
N21 N 0.0685(4) 0.2354(3) 0.0557(3) 0.0353(8) Uani 1 1 d . . .
C22 C -0.0616(5) 0.2573(5) 0.0299(4) 0.0412(11) Uani 1 1 d . . .
H22 H -0.0752 0.3045 0.0771 0.049 Uiso 1 1 calc R . .
C23 C -0.1741(6) 0.2145(6) -0.0611(5) 0.0573(16) Uani 1 1 d . . .
H23 H -0.2623 0.2320 -0.0761 0.069 Uiso 1 1 calc R . .
C24 C -0.1542(7) 0.1449(7) -0.1301(5) 0.078(3) Uani 1 1 d . . .
H24 H -0.2295 0.1135 -0.1930 0.094 Uiso 1 1 calc R . .
C25 C -0.0233(7) 0.1222(6) -0.1058(5) 0.072(2) Uani 1 1 d . . .
H25 H -0.0099 0.0740 -0.1523 0.086 Uiso 1 1 calc R . .
C26 C 0.0892(6) 0.1690(5) -0.0142(4) 0.0438(12) Uani 1 1 d . . .
C27 C 0.2399(6) 0.1640(4) 0.0171(4) 0.0383(10) Uani 1 1 d . . .
C28 C 0.2914(6) 0.1041(5) -0.0407(4) 0.0479(13) Uani 1 1 d . . .
F28 F 0.1977(5) 0.0363(4) -0.1291(3) 0.0780(13) Uani 1 1 d . . .
C29 C 0.4357(7) 0.1097(5) -0.0142(5) 0.0478(13) Uani 1 1 d . . .
H29 H 0.4677 0.0687 -0.0544 0.057 Uiso 1 1 calc R . .
C30 C 0.5316(6) 0.1793(4) 0.0750(4) 0.0422(11) Uani 1 1 d . . .
F30 F 0.6752(4) 0.1871(3) 0.1027(3) 0.0619(9) Uani 1 1 d . . .
C31 C 0.4897(5) 0.2410(4) 0.1353(4) 0.0361(10) Uani 1 1 d . . .
H31 H 0.5599 0.2887 0.1945 0.043 Uiso 1 1 calc R . .
C32 C 0.3406(5) 0.2324(4) 0.1077(3) 0.0309(9) Uani 1 1 d . . .
N41 N 0.4421(4) 0.4060(3) 0.2956(3) 0.0318(8) Uani 1 1 d . . .
C42 C 0.4923(6) 0.3901(4) 0.3889(4) 0.0408(11) Uani 1 1 d . . .
H42 H 0.4316 0.3367 0.4065 0.049 Uiso 1 1 calc R . .
C43 C 0.6284(7) 0.4489(5) 0.4595(4) 0.0540(15) Uani 1 1 d . . .
H43 H 0.6598 0.4359 0.5238 0.065 Uiso 1 1 calc R . .
C44 C 0.7172(7) 0.5266(5) 0.4340(5) 0.0570(16) Uani 1 1 d . . .
H44 H 0.8113 0.5665 0.4804 0.068 Uiso 1 1 calc R . .
C45 C 0.6682(6) 0.5460(5) 0.3403(4) 0.0486(13) Uani 1 1 d . . .
H45 H 0.7290 0.5993 0.3226 0.058 Uiso 1 1 calc R . .
C46 C 0.5274(5) 0.4865(4) 0.2710(4) 0.0352(10) Uani 1 1 d . . .
C47 C 0.4551(6) 0.5038(4) 0.1718(4) 0.0357(10) Uani 1 1 d . . .
C48 C 0.5171(7) 0.5827(4) 0.1302(4) 0.0453(12) Uani 1 1 d . . .
F48 F 0.6582(4) 0.6452(3) 0.1781(3) 0.0663(10) Uani 1 1 d . . .
C49 C 0.4406(8) 0.6008(5) 0.0397(5) 0.0538(15) Uani 1 1 d . . .
H49 H 0.4835 0.6547 0.0127 0.065 Uiso 1 1 calc R . .
C50 C 0.2990(8) 0.5365(5) -0.0089(4) 0.0528(15) Uani 1 1 d . . .
F50 F 0.2194(5) 0.5526(4) -0.1001(3) 0.0773(12) Uani 1 1 d . . .
C51 C 0.2316(6) 0.4554(4) 0.0259(4) 0.0417(11) Uani 1 1 d . . .
H51 H 0.1341 0.4131 -0.0118 0.050 Uiso 1 1 calc R . .
C52 C 0.3090(6) 0.4361(4) 0.1181(3) 0.0334(9) Uani 1 1 d . . .
P1 P 0.8633(2) 0.19135(13) 0.50991(12) 0.0528(4) Uani 1 1 d . . .
F1 F 0.8125(10) 0.2940(6) 0.4971(5) 0.162(4) Uani 1 1 d . . .
F2 F 1.0084(6) 0.2463(5) 0.4926(5) 0.122(2) Uani 1 1 d . . .
F3 F 0.9476(9) 0.2388(6) 0.6243(4) 0.138(3) Uani 1 1 d . . .
F4 F 0.9197(5) 0.0893(3) 0.5229(4) 0.0815(13) Uani 1 1 d . . .
F5 F 0.7207(7) 0.1295(7) 0.5203(5) 0.142(3) Uani 1 1 d . . .
F6 F 0.7848(5) 0.1486(5) 0.3938(3) 0.0896(15) Uani 1 1 d . . .
N61 N 0.5214(17) 0.1664(16) 0.7391(13) 0.244(10) Uani 1 1 d . . .
C62 C 0.4062(12) 0.1516(10) 0.7010(9) 0.127(5) Uani 1 1 d . . .
C63 C 0.2617(12) 0.1392(9) 0.6465(10) 0.140(6) Uani 1 1 d . . .
H63A H 0.2174 0.1644 0.6900 0.210 Uiso 1 1 calc R . .
H63B H 0.2108 0.0632 0.6152 0.210 Uiso 1 1 calc R . .
H63C H 0.2546 0.1813 0.5960 0.210 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C52 Ir1 N41 79.65(17) . . ?
C52 Ir1 N21 90.75(18) . . ?
N41 Ir1 N21 169.39(16) . . ?
C52 Ir1 C32 83.73(18) . . ?
N41 Ir1 C32 95.17(17) . . ?
N21 Ir1 C32 79.19(17) . . ?
C52 Ir1 C1 98.68(18) . . ?
N41 Ir1 C1 91.51(17) . . ?
N21 Ir1 C1 94.40(17) . . ?
C32 Ir1 C1 173.22(17) . . ?
C52 Ir1 C11 172.74(18) . . ?
N41 Ir1 C11 94.61(17) . . ?
N21 Ir1 C11 94.60(17) . . ?
C32 Ir1 C11 92.45(18) . . ?
C1 Ir1 C11 85.82(18) . . ?
N2 C1 N5 103.7(4) . . ?
N2 C1 Ir1 134.0(4) . . ?
N5 C1 Ir1 122.2(3) . . ?
C1 N2 C3 111.1(4) . . ?
C1 N2 C12 126.6(4) . . ?
C3 N2 C12 122.3(4) . . ?
C4 C3 N2 107.4(5) . . ?
C4 C3 H3 126.3 . . ?
N2 C3 H3 126.3 . . ?
C3 C4 N5 106.2(5) . . ?
C3 C4 H4 126.9 . . ?
N5 C4 H4 126.9 . . ?
C1 N5 C4 111.6(4) . . ?
C1 N5 C6 124.6(4) . . ?
C4 N5 C6 123.5(4) . . ?
N5 C6 N7 110.7(4) . . ?
N5 C6 H6A 109.5 . . ?
N7 C6 H6A 109.5 . . ?
N5 C6 H6B 109.5 . . ?
N7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C11 N7 C8 112.5(4) . . ?
C11 N7 C6 123.1(4) . . ?
C8 N7 C6 124.2(4) . . ?
C9 C8 N7 105.9(5) . . ?
C9 C8 H8 127.0 . . ?
N7 C8 H8 127.0 . . ?
C8 C9 N10 107.2(5) . . ?
C8 C9 H9 126.4 . . ?
N10 C9 H9 126.4 . . ?
C11 N10 C9 111.8(4) . . ?
C11 N10 C13 127.5(4) . . ?
C9 N10 C13 120.7(4) . . ?
N10 C11 N7 102.5(4) . . ?
N10 C11 Ir1 134.1(4) . . ?
N7 C11 Ir1 123.0(3) . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N10 C13 H13A 109.5 . . ?
N10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C22 N21 C26 117.9(4) . . ?
C22 N21 Ir1 123.9(3) . . ?
C26 N21 Ir1 117.4(3) . . ?
N21 C22 C23 123.7(5) . . ?
N21 C22 H22 118.2 . . ?
C23 C22 H22 118.2 . . ?
C22 C23 C24 118.1(5) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C25 C24 C23 119.3(6) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 121.1(6) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
N21 C26 C25 119.9(5) . . ?
N21 C26 C27 112.9(4) . . ?
C25 C26 C27 127.0(5) . . ?
C28 C27 C32 118.5(5) . . ?
C28 C27 C26 124.8(5) . . ?
C32 C27 C26 116.5(4) . . ?
F28 C28 C29 115.8(5) . . ?
F28 C28 C27 120.7(5) . . ?
C29 C28 C27 123.6(5) . . ?
C28 C29 C30 116.1(5) . . ?
C28 C29 H29 122.0 . . ?
C30 C29 H29 122.0 . . ?
F30 C30 C31 118.9(5) . . ?
F30 C30 C29 117.4(5) . . ?
C31 C30 C29 123.8(5) . . ?
C30 C31 C32 119.2(5) . . ?
C30 C31 H31 120.4 . . ?
C32 C31 H31 120.4 . . ?
C27 C32 C31 118.8(4) . . ?
C27 C32 Ir1 113.8(3) . . ?
C31 C32 Ir1 127.4(4) . . ?
C42 N41 C46 118.7(4) . . ?
C42 N41 Ir1 124.9(3) . . ?
C46 N41 Ir1 116.4(3) . . ?
N41 C42 C43 122.9(5) . . ?
N41 C42 H42 118.6 . . ?
C43 C42 H42 118.6 . . ?
C44 C43 C42 118.7(5) . . ?
C44 C43 H43 120.7 . . ?
C42 C43 H43 120.7 . . ?
C43 C44 C45 119.8(5) . . ?
C43 C44 H44 120.1 . . ?
C45 C44 H44 120.1 . . ?
C44 C45 C46 120.0(5) . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
N41 C46 C45 119.8(5) . . ?
N41 C46 C47 113.7(4) . . ?
C45 C46 C47 126.5(5) . . ?
C48 C47 C52 119.5(5) . . ?
C48 C47 C46 125.0(5) . . ?
C52 C47 C46 115.5(4) . . ?
F48 C48 C49 116.7(5) . . ?
F48 C48 C47 120.7(5) . . ?
C49 C48 C47 122.6(6) . . ?
C50 C49 C48 116.5(5) . . ?
C50 C49 H49 121.8 . . ?
C48 C49 H49 121.8 . . ?
C49 C50 C51 124.3(5) . . ?
C49 C50 F50 117.9(5) . . ?
C51 C50 F50 117.8(6) . . ?
C50 C51 C52 119.6(5) . . ?
C50 C51 H51 120.2 . . ?
C52 C51 H51 120.2 . . ?
C51 C52 C47 117.4(5) . . ?
C51 C52 Ir1 129.0(4) . . ?
C47 C52 Ir1 113.4(3) . . ?
F1 P1 F5 92.3(5) . . ?
F1 P1 F3 90.9(3) . . ?
F5 P1 F3 93.7(4) . . ?
F1 P1 F4 178.2(5) . . ?
F5 P1 F4 89.5(3) . . ?
F3 P1 F4 88.9(3) . . ?
F1 P1 F6 88.0(3) . . ?
F5 P1 F6 89.3(4) . . ?
F3 P1 F6 176.9(4) . . ?
F4 P1 F6 92.2(3) . . ?
F1 P1 F2 90.8(5) . . ?
F5 P1 F2 175.2(5) . . ?
F3 P1 F2 89.8(4) . . ?
F4 P1 F2 87.3(3) . . ?
F6 P1 F2 87.3(3) . . ?
N61 C62 C63 175(2) . . ?
C62 C63 H63A 109.5 . . ?
C62 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C62 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C52 2.043(5) . ?
Ir1 N41 2.052(4) . ?
Ir1 N21 2.053(4) . ?
Ir1 C32 2.063(4) . ?
Ir1 C1 2.112(5) . ?
Ir1 C11 2.114(5) . ?
C1 N2 1.350(6) . ?
C1 N5 1.362(6) . ?
N2 C3 1.389(7) . ?
N2 C12 1.459(7) . ?
C3 C4 1.331(8) . ?
C3 H3 0.9400 . ?
C4 N5 1.388(6) . ?
C4 H4 0.9400 . ?
N5 C6 1.449(6) . ?
C6 N7 1.451(6) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
N7 C11 1.367(6) . ?
N7 C8 1.382(6) . ?
C8 C9 1.337(9) . ?
C8 H8 0.9400 . ?
C9 N10 1.384(7) . ?
C9 H9 0.9400 . ?
N10 C11 1.359(6) . ?
N10 C13 1.451(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
N21 C22 1.359(6) . ?
N21 C26 1.368(7) . ?
C22 C23 1.369(7) . ?
C22 H22 0.9400 . ?
C23 C24 1.378(9) . ?
C23 H23 0.9400 . ?
C24 C25 1.373(10) . ?
C24 H24 0.9400 . ?
C25 C26 1.381(8) . ?
C25 H25 0.9400 . ?
C26 C27 1.465(7) . ?
C27 C28 1.397(7) . ?
C27 C32 1.400(7) . ?
C28 F28 1.360(7) . ?
C28 C29 1.367(8) . ?
C29 C30 1.381(8) . ?
C29 H29 0.9400 . ?
C30 F30 1.352(6) . ?
C30 C31 1.368(8) . ?
C31 C32 1.404(6) . ?
C31 H31 0.9400 . ?
N41 C42 1.352(6) . ?
N41 C46 1.364(6) . ?
C42 C43 1.378(8) . ?
C42 H42 0.9400 . ?
C43 C44 1.369(9) . ?
C43 H43 0.9400 . ?
C44 C45 1.373(9) . ?
C44 H44 0.9400 . ?
C45 C46 1.404(7) . ?
C45 H45 0.9400 . ?
C46 C47 1.464(7) . ?
C47 C48 1.394(7) . ?
C47 C52 1.420(7) . ?
C48 F48 1.354(7) . ?
C48 C49 1.373(9) . ?
C49 C50 1.366(10) . ?
C49 H49 0.9400 . ?
C50 C51 1.370(8) . ?
C50 F50 1.379(7) . ?
C51 C52 1.404(7) . ?
C51 H51 0.9400 . ?
P1 F1 1.554(5) . ?
P1 F5 1.554(6) . ?
P1 F3 1.566(5) . ?
P1 F4 1.576(4) . ?
P1 F6 1.577(5) . ?
P1 F2 1.603(6) . ?
N61 C62 1.069(15) . ?
C62 C63 1.372(14) . ?
C63 H63A 0.9700 . ?
C63 H63B 0.9700 . ?
C63 H63C 0.9700 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C52 Ir1 C1 N2 -21.2(5) . . . . ?
N41 Ir1 C1 N2 58.6(5) . . . . ?
N21 Ir1 C1 N2 -112.6(5) . . . . ?
C32 Ir1 C1 N2 -131.5(13) . . . . ?
C11 Ir1 C1 N2 153.1(5) . . . . ?
C52 Ir1 C1 N5 157.2(4) . . . . ?
N41 Ir1 C1 N5 -123.1(4) . . . . ?
N21 Ir1 C1 N5 65.7(4) . . . . ?
C32 Ir1 C1 N5 46.8(15) . . . . ?
C11 Ir1 C1 N5 -28.6(4) . . . . ?
N5 C1 N2 C3 0.1(5) . . . . ?
Ir1 C1 N2 C3 178.7(4) . . . . ?
N5 C1 N2 C12 -178.9(5) . . . . ?
Ir1 C1 N2 C12 -0.3(8) . . . . ?
C1 N2 C3 C4 -0.1(6) . . . . ?
C12 N2 C3 C4 179.0(5) . . . . ?
N2 C3 C4 N5 0.0(6) . . . . ?
N2 C1 N5 C4 -0.1(5) . . . . ?
Ir1 C1 N5 C4 -178.9(3) . . . . ?
N2 C1 N5 C6 173.4(4) . . . . ?
Ir1 C1 N5 C6 -5.4(6) . . . . ?
C3 C4 N5 C1 0.0(6) . . . . ?
C3 C4 N5 C6 -173.5(5) . . . . ?
C1 N5 C6 N7 52.7(6) . . . . ?
C4 N5 C6 N7 -134.6(5) . . . . ?
N5 C6 N7 C11 -55.1(6) . . . . ?
N5 C6 N7 C8 130.0(5) . . . . ?
C11 N7 C8 C9 0.4(6) . . . . ?
C6 N7 C8 C9 175.9(5) . . . . ?
N7 C8 C9 N10 0.1(6) . . . . ?
C8 C9 N10 C11 -0.6(7) . . . . ?
C8 C9 N10 C13 179.0(5) . . . . ?
C9 N10 C11 N7 0.8(6) . . . . ?
C13 N10 C11 N7 -178.7(5) . . . . ?
C9 N10 C11 Ir1 173.4(4) . . . . ?
C13 N10 C11 Ir1 -6.1(8) . . . . ?
C8 N7 C11 N10 -0.8(6) . . . . ?
C6 N7 C11 N10 -176.3(4) . . . . ?
C8 N7 C11 Ir1 -174.4(4) . . . . ?
C6 N7 C11 Ir1 10.1(6) . . . . ?
C52 Ir1 C11 N10 -16.4(16) . . . . ?
N41 Ir1 C11 N10 -53.8(5) . . . . ?
N21 Ir1 C11 N10 120.9(5) . . . . ?
C32 Ir1 C11 N10 41.6(5) . . . . ?
C1 Ir1 C11 N10 -145.0(5) . . . . ?
C52 Ir1 C11 N7 155.0(12) . . . . ?
N41 Ir1 C11 N7 117.6(4) . . . . ?
N21 Ir1 C11 N7 -67.7(4) . . . . ?
C32 Ir1 C11 N7 -147.1(4) . . . . ?
C1 Ir1 C11 N7 26.4(4) . . . . ?
C52 Ir1 N21 C22 -84.9(4) . . . . ?
N41 Ir1 N21 C22 -109.8(8) . . . . ?
C32 Ir1 N21 C22 -168.3(4) . . . . ?
C1 Ir1 N21 C22 13.9(4) . . . . ?
C11 Ir1 N21 C22 100.1(4) . . . . ?
C52 Ir1 N21 C26 84.8(4) . . . . ?
N41 Ir1 N21 C26 59.9(10) . . . . ?
C32 Ir1 N21 C26 1.4(4) . . . . ?
C1 Ir1 N21 C26 -176.4(4) . . . . ?
C11 Ir1 N21 C26 -90.2(4) . . . . ?
C26 N21 C22 C23 1.7(9) . . . . ?
Ir1 N21 C22 C23 171.4(5) . . . . ?
N21 C22 C23 C24 0.3(11) . . . . ?
C22 C23 C24 C25 -0.7(13) . . . . ?
C23 C24 C25 C26 -1.0(14) . . . . ?
C22 N21 C26 C25 -3.3(9) . . . . ?
Ir1 N21 C26 C25 -173.7(6) . . . . ?
C22 N21 C26 C27 171.7(5) . . . . ?
Ir1 N21 C26 C27 1.3(6) . . . . ?
C24 C25 C26 N21 3.0(12) . . . . ?
C24 C25 C26 C27 -171.2(8) . . . . ?
N21 C26 C27 C28 -178.7(5) . . . . ?
C25 C26 C27 C28 -4.2(10) . . . . ?
N21 C26 C27 C32 -4.8(7) . . . . ?
C25 C26 C27 C32 169.8(7) . . . . ?
C32 C27 C28 F28 179.8(5) . . . . ?
C26 C27 C28 F28 -6.4(9) . . . . ?
C32 C27 C28 C29 -1.1(9) . . . . ?
C26 C27 C28 C29 172.8(6) . . . . ?
F28 C28 C29 C30 179.3(5) . . . . ?
C27 C28 C29 C30 0.1(9) . . . . ?
C28 C29 C30 F30 -179.6(5) . . . . ?
C28 C29 C30 C31 -0.4(8) . . . . ?
F30 C30 C31 C32 -179.2(4) . . . . ?
C29 C30 C31 C32 1.7(8) . . . . ?
C28 C27 C32 C31 2.3(7) . . . . ?
C26 C27 C32 C31 -172.1(5) . . . . ?
C28 C27 C32 Ir1 -179.7(4) . . . . ?
C26 C27 C32 Ir1 5.9(6) . . . . ?
C30 C31 C32 C27 -2.6(7) . . . . ?
C30 C31 C32 Ir1 179.7(4) . . . . ?
C52 Ir1 C32 C27 -95.9(4) . . . . ?
N41 Ir1 C32 C27 -174.9(3) . . . . ?
N21 Ir1 C32 C27 -3.9(3) . . . . ?
C1 Ir1 C32 C27 15.3(15) . . . . ?
C11 Ir1 C32 C27 90.3(4) . . . . ?
C52 Ir1 C32 C31 81.9(4) . . . . ?
N41 Ir1 C32 C31 2.9(4) . . . . ?
N21 Ir1 C32 C31 173.9(4) . . . . ?
C1 Ir1 C32 C31 -166.9(12) . . . . ?
C11 Ir1 C32 C31 -91.9(4) . . . . ?
C52 Ir1 N41 C42 171.5(4) . . . . ?
N21 Ir1 N41 C42 -163.1(7) . . . . ?
C32 Ir1 N41 C42 -105.8(4) . . . . ?
C1 Ir1 N41 C42 73.0(4) . . . . ?
C11 Ir1 N41 C42 -13.0(4) . . . . ?
C52 Ir1 N41 C46 -10.4(3) . . . . ?
N21 Ir1 N41 C46 15.0(10) . . . . ?
C32 Ir1 N41 C46 72.3(4) . . . . ?
C1 Ir1 N41 C46 -108.9(4) . . . . ?
C11 Ir1 N41 C46 165.1(4) . . . . ?
C46 N41 C42 C43 -2.6(8) . . . . ?
Ir1 N41 C42 C43 175.4(5) . . . . ?
N41 C42 C43 C44 -0.2(10) . . . . ?
C42 C43 C44 C45 1.4(10) . . . . ?
C43 C44 C45 C46 0.1(10) . . . . ?
C42 N41 C46 C45 4.1(7) . . . . ?
Ir1 N41 C46 C45 -174.1(4) . . . . ?
C42 N41 C46 C47 -173.6(4) . . . . ?
Ir1 N41 C46 C47 8.2(5) . . . . ?
C44 C45 C46 N41 -2.9(8) . . . . ?
C44 C45 C46 C47 174.5(6) . . . . ?
N41 C46 C47 C48 178.3(5) . . . . ?
C45 C46 C47 C48 0.7(9) . . . . ?
N41 C46 C47 C52 0.9(6) . . . . ?
C45 C46 C47 C52 -176.7(5) . . . . ?
C52 C47 C48 F48 -177.2(5) . . . . ?
C46 C47 C48 F48 5.5(8) . . . . ?
C52 C47 C48 C49 2.3(8) . . . . ?
C46 C47 C48 C49 -175.0(5) . . . . ?
F48 C48 C49 C50 179.0(5) . . . . ?
C47 C48 C49 C50 -0.5(9) . . . . ?
C48 C49 C50 C51 -1.2(9) . . . . ?
C48 C49 C50 F50 -179.9(5) . . . . ?
C49 C50 C51 C52 1.1(9) . . . . ?
F50 C50 C51 C52 179.7(5) . . . . ?
C50 C51 C52 C47 0.8(7) . . . . ?
C50 C51 C52 Ir1 -173.9(4) . . . . ?
C48 C47 C52 C51 -2.3(7) . . . . ?
C46 C47 C52 C51 175.2(4) . . . . ?
C48 C47 C52 Ir1 173.1(4) . . . . ?
C46 C47 C52 Ir1 -9.3(5) . . . . ?
N41 Ir1 C52 C51 -174.8(5) . . . . ?
N21 Ir1 C52 C51 9.7(5) . . . . ?
C32 Ir1 C52 C51 88.7(5) . . . . ?
C1 Ir1 C52 C51 -84.9(5) . . . . ?
C11 Ir1 C52 C51 147.2(12) . . . . ?
N41 Ir1 C52 C47 10.4(3) . . . . ?
N21 Ir1 C52 C47 -165.1(4) . . . . ?
C32 Ir1 C52 C47 -86.1(4) . . . . ?
C1 Ir1 C52 C47 100.3(4) . . . . ?
C11 Ir1 C52 C47 -27.6(15) . . . . ?
